The Red Dragon Emperor & The Red Queen
by BLS91090
Summary: In this crossover of High School DxD and Hundred, Issei Hyoudou meets Claire Harvey! Together, they will share adventures, and then romance later on. Includes some comedy, as well. Some events of the Hundred series are rewritten, with Issei replacing Hayato. Also includes a bonus 'harem chapter' at the end. Rated M for some language, adult content and lemons.
1. Chapter 1

Issei Hyoudou, the Red Dragon Emperor and the Harem King, arrived at the university battleship called the Little Garden. He was here for a vacation, to be away from the ORC and whatnot. It was still around morning time after he exited his plane.

"All this atop an aircraft carrier? That's pretty hard to believe..." Issei murmured as he had a tour of the place.

Boasting a surface area of more than four square kilometers, there was a town atop this aircraft carrier. Simply by scale alone, no one could ever find anything in the entire world that could be its equal. In order to preserve its freedom, Little Garden never stopped sailing. For something of this scale, this was undoubtedly a world's first. This ship wasn't attached to any nation.

Little Garden had its headquarters in the federal state of Liberia, where the production company responsible for developing fighters, military ships, and so on, was located. Even though the Warslan company was a PMC (private military company _)_ , they had built Little Garden themselves to serve as a base both for battling the Savage and for the research and development of the Hundred weapon. For the sake of training Slayers—those who wielded the Hundred—no expense was spared when it came to this huge aircraft carrier. That rationale had manifested itself in every aspect of its design.

There was one main reason Issei was here: to meet the queen known as Claire Harvey. He had read up on her previously: Claire's 'Hundred' boasted extreme mobility, and true to its nature as a Dragoon-type model, could freely employ heavy weaponry. Its name, carrying the meaning of 'Noble War Princess', was Alystherion. Counting from when Little Garden and the Bugeika had been founded two years prior, she had never once lost, and so she'd come to be known as the 'Perfect Queen'.  
She was someone who had battled twelve Savages as a lone Slayer in the two years since her admission. The total number of sorties against the Savage to date numbered 17, and thus she'd not only participated in nearly every battle, but she'd dealt the killing blow in over half of the battles she'd taken part in. Her merits in battle had earned her the nickname 'Rose Guardian'.

There was a ceremony going on for the Little Garden students in the auditorium. Issei was on the sidelines and watching, waiting for Claire to show up. He had even gotten autograph requests by boys and girls who were familiar with him. He found it quite amusing.

Lots of boring stuff went on first, but then...

A girl with brown hair and glasses named Erica Candle was making an announcement. "Next, a word of greeting from the captain/commander of the Academy Battleship, Little Garden; the supervisor of the elementary, middle, and high school section of the Bugeika infantry; our student council president; and she, who holds the position of Queen. I'd like to introduce you all to Claire Harvey!"

A nervous energy filled the auditorium. Issei, however, was excited!

Appearing from the side of the stage, an extremely beautiful girl walked up to the stand. It was clear from the way she walked that she was definitely the princess type. She was a student council president who holds immense power. Her curly blonde hair, blue eyes, incredible body and massive breasts made for quite the sight. She was the captain of the little city garden, and the president of all the students in the General Division.

Excited cheers could be heard with Claire's entry. It wasn't just the students of the Bugeika; the students of the other schools and the people of Little Garden in general idolize Claire as well. She was tremendously popular.

Claire Harvey was the highest-ranked Slayer in Little Garden, from the United States of Liberia; she was called the Queen. Despite having been called a 'Queen', she was of an age comparable to Issei and his friends. That said, she had a strong, keen gaze and an aura of majestic dignity which made it clear the title was well deserved.

 _'Damn... She's really hot!'_ Issei thought as he looked at the beauty. He was taken aback by how gorgeous she was, for a human. He was definitely gonna enjoy meeting her when he had a chance.

Queen Claire finally reached the podium. Silence immediately filled the room as the audience awaited her words. "Hello students, my name is Claire Harvey." Her voice was elegant and nice to listen to.

 _'Prez's thighs are amazingly plump,_ ' Issei thought. ' _She reminds me of my girls back home!'_

However, before Claire could continue...

"E-Excuse me―!" "Sorry for being late!"

The sound of a door opening could be heard, followed by two voices echoing throughout the silent room. In a flash, everyone's gaze spun from Claire, on the stage, to the entrance, where the voices had originated. There stood two girls of Oriental lineage. They wore Bugeika uniforms, the collars of which had a noticeable absence: badges.

"Arriving late on your very first day? You two sure are brave." From her spot on the stage, Claire cast the two a withering glare, leaving them trembling in fear.  
"Um… we went out earlier this morning to pick up a few things at the shopping center, but it took more time than expected―"

"I didn't ask for your excuses. You were warned in advance of the need to be punctual." Claire's tone was flat, drowning out the girl's words. Sternly, she continued, extending her left index finger and pointing at the girls, declaring firmly "Little Garden has no need for those who can't keep their word. Promptly pack your belongings and leave."

The girls sighed in defeat and left.

This impressed Issei. _'Man... she's tough, that's for sure.'_

Claire cleared her throat, then got into a big speech. "The single most important duty is, of course, to battle the Savage, however," Claire added in a tone which suggested such a thing was only natural, "Although Slayers belong to the Warslan company from the moment they enroll in the Bugeika, they are nevertheless still students, and thus participation in such duties is not mandatory; it is up to each student's own judgment. However, the way I see things…"

After a short pause, Claire continued with a serious expression.

"It's a matter of noblesse oblige. Those with power have an obligation to wield that power for the sake of those without. Such a thing is only natural. This is why the Warslan company provides suitable compensation for those who hold such power."

Issei was even more impressed now. _'I like her already!'_

* * *

After the ceremony was over, Issei had a chance to do a meet-and-greet with Claire.

"It's great to finally meet you in person, Claire Harvey." Issei grinned and shook her hand.

"Nice to meet you as well, Issei Hyoudou." Claire shook his hand back; she grasped tightly the hand presented by Issei. A tie, a prove of friendship. A nice handshake. "As you said, I am Claire Harvey, the representative of Little Garden. Is it fine if I call you Mr. Hyoudou?"

"Yeah, that's fine with me." Their hands soon parted.

Claire then thought for a moment. She thought back on news reports of the Red Dragon Emperor. "...I've heard of you, actually. Your reputation precedes you, as a powerful fighter."

"Well, thanks for saying so!" Issei grinned more. "Oh and... I gotta say, you're as tough as they say." Issei told her, regarding the incident earlier.

"I am indeed. Those girls had butted in so belligerently... By all rights, I should have expelled them."

Issei chuckled. "Damn!" He enjoyed talking with her. "So you're the daughter of the family which runs the Warslan Company, and by extension, the Little Garden?" Issei asked her.

Claire nodded. "Yes. That means I wield an amazing degree of authority around here."

"I can see that, since you're the captain, the Queen, and student council president." Issei chuckled.

"Indeed. And I am not the student council president and captain because of who my parents are. That is a mistake, if anyone ever told you that. I do not stand here now because my father manages the Warslan Company. No, I am the student council president who oversees all students of Little Garden—primary, middle, high, and Bugeika—and captain because I am the Queen who holds the top rank among the Bugeika student body. More precisely, I am the one who has attained the throne of Queen."

"Wow, that's a lot to take in! Thanks for the info, though." Issei realized that Claire might be busy. "Oh, sorry for taking your time."

"It's fine. Well, I must attend to my duties now." Claire was about to leave and turned around.

Issei had something to ask her first. "Can I ask you a question before you go?"

"Go ahead. What is it?" Claire turned her head to look back at him.

"Will you join in this bikini contest this summer at Banoi island? I'm hosting it!"

Claire turned back around looked at him directly. "...That's quite a request, I'd have to say. I'll have to think about it." Claire had her hand under her chin and thought for a moment.

 _'I hope she says yes.'_

"...Sure, why not?"

"Great! Here is the info." Issei gave her a piece of paper with written information on it.

Claire looked at it, then looked back at Issei. "Would it be alright if I added a condition?" Claire asked.

"Yeah, sure."

"I don't want to leave until I have completed all my work. And... winning a contest and enjoying beach activities... this is killing two birds with one stone, really."

Issei was surprised. "You're saying you've already won?"

She showed a cocky smile. "I'm quite confident, let's put it that way."

Issei grinned. "I like your spirit. Well... See ya, Claire!" Issei waved and took off.

"Goodbye, for now." Claire left as well.

* * *

Student council meetings began at 8:15 am precisely at the school. Everyone in the club was expected to be there on time.

The door opened to admit the student council president, Claire Harvey. "I apologize for the wait." Meetings would always begin with Claire looking gorgeous as always. A nervous energy filled the room, because she was indeed a student council president who held immense power. She had tea, folders, papers, pens, a computer, and files on the desk near her. "First things first, shall we have some black tea? Erica, the usual, if you would."

"Understood." As Claire lowered herself into the remaining chair, Erica made her way from seat to seat, filling their cups with black tea.

Claire then cleared her throat and officially began the meeting. "Hello students, my name is Claire Harvey." She was very elegant. "The Student Council President is the highest-ranking officer of a student government group or a student union association at the high school, college, or university level. It is in Elementary schools, too." Claire continued, "A student government president is different from a class president. Class presidents represent a specific grade level of students, while a student body president represents students of all grade levels."

"Class presidents are common in middle and high schools and some colleges and universities in the U.S. A close equivalent would be a Freshman, Sophomore, Junior, or Senior class representative or senator." She explained the council stuff with an authoritative tone. She continued on with more lectures that were required.

Issei was outside the door to the clubroom. He had his arms crossed as he listened to Claire. _'She's really something.'_ He smiled to himself.

* * *

Later in the day, Issei found Claire practicing by herself at the school's outdoor training area. She seemed very focused, even though she had no one to practice with. She was wearing a Variable Suit; it was the same shade of red her uniform had been.

 _'She is really hot, in any uniform!'_ He decided to ask her for a friendly challenge. "Hey Claire, do you wanna spar with me?" Issei approached her, keeping a fair distance between the two of them.

Claire stopped in her tracks and saw Issei there. "Oh, hello." She wiped her forehead. "That sounds interesting." She smirked lightly and turned her attention to him fully. "Let's see what you got."

"Sure thing!" Issei grinned. He summoned his red-colored boosted gear to his arm. "BOOST!" The sound of Ddraig was heard.

Claire was confused at this. "What was that noise? And what is that on your arm?"

"You know how I have a rep as a great fighter? Well, this bad-boy is part of it!" Issei boosted up again. "And inside my gear is a dragon named Ddraig. Cool, right?"

 _"I am the dragon, Ddraig!"_ Ddraig's voice was heard from the gear.

Claire blinked several times with a surprised face. "How on Earth?" Claire stared in wonder. "...Quite confusing, and odd." A chuckle slipped out of Claire's mouth, then she continued, "In any case, could you not stare?"

"…Eh?" Issei blinked.

"You were eyeing me right now… with that lewd gaze…"

"Oh, well...heheh..." Issei chuckled and rubbed the back of his head. He couldn't deny it. It was true that he was fascinated, being the perv and Harem King that he was!

The Variable Suit clung to Claire's body, showing off her well-developed, womanly curves. It also exposed more skin than a student uniform. The two big bulges of her breasts and her figure, which made it impossible to deny her femininity, were so amazing that Issei couldn't help it!

"…I was just joking. Well then, shall I deploy my Hundred?" Claire didn't bother to wait for a reply. She flipped the Hundred she grasped in her hand lightly into the air. "HUNDRED ON!" Alongside her shout, the Hundred released an emerald green light which transformed into six, red gun pods.

"Interesting transform!" Issei had boosted one more time.

"Come, Issei Hyoudou! Show me what you can do!" Claire shouted as she fired Alystherion in his direction.

Issei grinned and jumped in the air, moving swiftly towards Claire. Dodging the six beams coming from Alystherion, he closed the gap between Claire and himself in no time.

"Wha―?!" Claire was caught off-guard, and her eyes widened in surprise. "Y-You're so fast...!"

Instead of firing a boosted blast, Issei had something devious and pervy planned for Claire! He touched her shoulder, and a magic circle appeared at the point of contact.

"What the...?" Claire had no idea what Issei was up to.

"Dress Break!" Issei yelled out, snapping his fingers.

Claire's variable suit then blew up before her eyes! "KYA―!" Claire shrieked, kneeing on the ground with her arms covering her naked breasts. "Why you...!"

Issei grinned and had a thumbs up! "Dress Break: gotta love it!" Using his quick eyes, he had managed to see Claire's breasts before she covered them. ' _Damn, her oppai are nice!'_

"Y-You… What on Earth do you think you're…" Claire's face was dyed a deep red as she raised her eyebrows. Frankly, it was incredibly embarrassing. And she had never seen this kind of thing before.

No one else saw, though. So Issei was lucky this time!

* * *

Late that night, Claire being the student council president was burning the midnight oil in the student council room of the Bugeika school building.  
She had matters which had to be resolved before the day was over, as well as a stack of official paperwork to be signed. The contents of the papers she held in her hands never entered her consciousness. She simply could not stop thinking about Issei Hyoudou.

With regards to the outcome of the earlier sparring match, her pride as the undefeated Queen with a two-year reign had almost been demolished. And by...a dress break?!

Thankfully, it was only considered a sparring match and not considered a full-fledged match.

"Claire-sama. Claire-sama…" A voice called her from her reverie. Erica had approached her without her realizing.

"…How long have you been there?" Claire turned to look at her.

"Since a moment ago. I called you once already, but you didn't respond, so I called once more."

"I apologize. I was lost in thought." Claire turned her gaze to Erica's hands. She was holding a teapot and a cup. "Black tea, is it? Thank you."

Erica placed the tea cup on Claire's desk before continuing. "Would you like anything to go with your tea?"

"No...thank you, though." Claire sighed to herself.

Erica had something to ask. "What's wrong, Claire-sama? You seem out of it today, ever since that guy Issei came to visit."

Claire was too embarrassed to say exactly what happened. She made a shorter version of it. "Well...we had a sparring match. And he won..."

Erica's expression clouded in an instant. "…Please don't worry about it too much. If it had been an ordinary duel, then it would unmistakably have been Claire-sama's victory."

"I'm not worrying about that." Claire then thought about the upcoming Banoi contest that was coming up in a few days. "Hmm.." Claire seemed deep in thought, her hand under her chin.

Erica tilted her head to the side, wondering what Claire was thinking about.


	2. Chapter 2

Welcome to Banoi Island, a wild and untamed atoll off the coast of Papua New Guinea. The waters were as clear and blue as the skies. The air was fresh, the beaches were clean, and the world-famous Banoi Resort stood marvelously against the scenic mountainous background. From the lush rain forests to the mountain highlands to the white sandy beaches, Banoi is considered the pearl in the necklace of the Oceania Archipelago. For many, it is Heaven on Earth — a place of peace and pristine beauty where travelers can leave the worries and cares of the world behind.

You couldn't talk about Banoi without mentioning the Royal Palms Resort, a luxurious five-star hotel on Banoi. Nestled in the hills above the most pristine white sand beaches in the South Pacific, the Royal Palms Resort offers every luxury. The acclaimed architecture of the five-star resort blends seamlessly with the natural beauty of Banoi Island. The Royal Palms Resort offers exceptional service and every modern amenity. The 127 spacious, climate-controlled rooms offer a spectacular view of either the jungle highlands or the Pacific Ocean. All the first-class accommodations offer a private balcony or a patio where the guests can enjoy a cocktail and enjoy warm, equatorial breezes scented with the heady perfume of rare tropical blossoms. All things considered, it was a nice place.

It was bright, sunny, and warm; a more beautiful day could not be asked for. A perfect day to lay out on the sand or splash around in the water. And, an excellent day to enjoy the view.

Issei was getting ready to host the 2017 edition of the Women's Bikini Contest at Banoi Island's Beach and Resort area. It would be recorded, to be released later on television as a TV special. He had a meet-and-greet with the girls who were in the contest before it would begin.

He asked the girls for hugging and kissing permission before the show; most would accept just for the fact that they would appear on TV, and others were against the idea altogether. Issei himself wanted to do it for obvious reasons, but the producers of the program had asked him to do it.

Claire arrived on the island via her family's helicopter. She was still in her school uniform and had a giant bag filled with her stuff. "This island is simply gorgeous." She admired the place. She then spotted Issei near a bungalow bar; she approached him. "Hello, Issei Hyoudou."

"Hey, Claire! ...Huh? You're not in your bikini yet?" Issei wondered.

"I've only just arrived here, actually. I will change shortly." Claire explained to him. "Any further questions?" Claire asked Issei regarding the contest.

Issei did have the infamous question to ask. "It is okay if I give you kisses during the contest?"

Claire was a bit surprised and blushed. "W-Why do you ask?" The look 'That's unheard of' was written all over Claire's face.

"Well I do it for the contest, ya know? Just for the show's sake, because the producers and whatnot asked me." Issei chuckled a little.

Claire thought for a moment. "Kissing… It's a sign of deep affection in Liberia, to show dear embodiment, and..." She then continued on with an air of innocence, "It would be rather harsh of me to hold back the competition or it's traditions, so... I'll accept the request."

"Awesome! Let's do a practice kiss now." Issei leaned over to her.

Claire blushed more and barely accepted. "V-Very well, then..." As Claire nodded, signalling Issei's permission to proceed, she leaned in too.

They kissed on the lips. Issei's mouth felt her lips; it was particularly sweet and especially soft. They pulled away after.

"Y-You know, you're my real first kiss ever..." Claire was embarrassed and she blushed. ' _Ara, what a coincidence.'_

"Oh really? Sweet!" Issei grinned at the goal that he reached. _'I kissed the mouth of the president! Her lips are so soft!'_

"It was...nice." Claire muttered in satisfaction, still with a reddened face.

[Some time later]

After the contest/show officially began, Claire was up first to the front stand. She looked incredible in her red bikini and with her hair down. All the guys want to do her, and all the girls want to be her!

"Ms. Claire Harvey! How are you, gorgeous?" Issei smiled and leaned in for a kiss. He was only in his swimming trunks during the show.

Claire and Issei kissed on lips as they shook hands. "Hello, Mr. Hyoudou. I'm doing fine, thank you for asking." Claire was beautiful and mature as always. "Do you like my swimsuit?" She had asked him in a teasing way.

"Hell yeah I do!" They shared a hug together, enjoying the soft big breasts that pressed against him. "Good luck in the contest!" Issei puckered up for one more kiss with her in his arms.

"Thank you again." Claire kissed his lips again. "I'm sure I will be victorious." Claire had to hid her blush from Issei's kisses, since she was still getting used to it, and because the contest was being recorded for TV. She walked away, but not before telling off a girl that said she would win instead of Claire. "I'm afraid that's not going to happen." She dissed the chick.

Issei overheard this and grinned to himself. ' _Claire's got spirit!'_

[Some time later]

The contest was very close. So many beautiful women, so it was very hard to choose in the end. In fact, there was about 87 women in total!

However, Claire Harvey ended up being the winner. She won a ribbon, a trophy, a crown, and a $1,500 dollar award. She went up to Issei at the main stand, who congratulated her with a kiss and a hug and with the rewards. In fact, Issei was the one who personally chose her as the pick.

"Congrats, Ms. Claire Harvey!" Issei grinned with a microphone as he spoke. He had his arm around Claire as they had a brief conversation.

"Thank you. I felt I deserved to win, but all the other ladies did well. It was a good battle in the end." Claire spoke while holding a mic as well, and smiling beautifully.

"Well ya heard it, ladies and gents!" Issei grinned again. "Thanks for attending our contest! Have a nice day!" After he announced that to the audience, he gave one last kiss to the president's lips and then a hug, and then let her go with her rewards. He kept thinking about Claire's breasts during the contest, as expected of him. _'Man... Prez's breasts are really wonderful. They are very soft, too!'_

And with that, everyone could go back to their usual beach activities and whatnot; such as volleyball, swimming, fishing, surfing, and sharing watermelon, among other many others.

[Some time later]

Later on in the day, Claire needed sunscreen on her body, since it was sun sensitive. Erika normally did it for her, but she wasn't present. So instead, Claire asked Issei! "Issei, would you mind applying this lotion on me?" The student president sure was a beauty.

"No problem at all, Claire!" Issei grinned with a pervy face.

"Thank you, you're kind." Claire laid on her chair. "Make sure to get it all over. My skin is sensitive." She had a drink on the table near her. "Don't try anything funny, though." She sent him a sharp look.

Issei nodded with a goofy look on his face. "Don't worry!" He then proceeded to oil up the beautiful Claire Harvey! A lucky son of a bitch. _'She's got a hell of a body!'_ He oiled up Claire from her feet to her neck. _'Damn, her skin is soft and smooth!'_ At times, he sat down on Claire's butt and his crotch was pressed against it. He massaged Claire's hot legs several times over. He would also sit with one of Claire's legs resting over his lap as he rubbed her leg. _'Prez's body is really soft!'_

Dudes that saw this were jealous enough to kill him! Too bad they couldn't do anything.

"You want me to do the front, too?" Issei asked, somewhat bravely.

Claire turned her head to him with a raised eyebrow. After thinking a bit, she told him, "Very well. I trust you... Just don't try anything, remember?" She flipped over, her eyes closed.

Issei grinned big and began to oil Claire's beautiful body up front! ' _So awesome, dude!_ ' He did one more round of full body oiling, then finally stopped. "There you go."

Claire smiled and took the lotion bottle. "Thank you, Issei. Although it seemed more like I was getting a massage from you, if anything." She chuckled.

"Yeah, well...what are ya gonna do?" Issei chuckled, too.

Suddenly, a kid pushed Issei from behind! "Hahahahahaha!" The obnoxious kid laughed and ran away.

Issei ended up landing face-first into Claire's large breasts! "Mmmpppff!" His face was pressed firmly inside them. _'I-I fell on the student council president...! She's a beauty... and her breasts are massive!'_ He felt her extremely soft body.

Claire was extremely surprised and caught-off guard. "Issei Hyoudou-! What are you-! HYYAAAA!" She gasped and blushed madly.

 _'Oh man~ The oppai~!_ ' Issei enjoyed himself a lot, but knew he had to surface to explain the situation. But...he didn't feel like it! Instead, his face stayed inside those fantastic soft boobies, ignoring Claire's constant moving around and cries.

"KYA―!" Claire shrieked more. "Th―! Issei Hyoudou―! You, where do you think you're touching?!" She realized that Issei was squeezing her breasts now! "KYAA—!" The president's shriek continued.

Issei figured he could get some feels in before leaving. _'Damn, these are soft and incredible!'_ He squeezed and motor-boated Queen Claire Harvey's voluminous breasts. "Brbrbrbrbrbrbrrrrbrbrbr!" Issei's eyes reflected two pink beautiful protrusions.

"Y-You… What on Earth do you think you're…" Claire's face was dyed a deep red and she shrieked more. "Han―!" She used all her strength to thrust Issei away with both hands and then forcefully stood up, Claire's blushing face still visible.

"Whoa!" Issei released his hands from her breasts and flew back into the sand.

She pointed her finger at him intensely with tears in her eyes. "For someone else to touch my b-breasts… This hasn't happened once before…" Trying to preserve her dignity as the Queen, Claire crossed both arms in front of her breasts, her shoulders quivering violently. "You've got some nerve... haven't you, Issei Hyoudou?" She was ready for a fight. "You'll now receive the punishment for playing with my breasts!"

"C-Claire, wait! Don't do this shit on Banoi island!" Issei had a good point. "Besides, I'm sorry for what happened! A kid pushed me!"

"My breasts are not so cheap that you can simply apologize―!" Claire still wanted retribution. Her body trembled with anger. ' _H-how shameless of him—!'_

A random guy was laughing heartily. "It must've been great, rubbing the Prez's breasts. They were huge, right?"

They were huge indeed. And very soft.

By now, a bunch of people were watching the scene. What a mess this was.

* * *

A few days later, Claire was in her office doing more paperwork. The memory of Issei's touch crossed her mind a lot. Claire reddened.  
She lifted her tea cup as if to demonstrate her composure, though she achieved the opposite effect as her hands were trembling. She couldn't stop thinking about him!

It went without saying that her chest had never once been touched by a member of the opposite sex. For something like that to happen – in front of the public even! It was a complete disgrace. But... _'I wonder what this is I'm feeling…'_ The reason for the pounding of her heart. What she was feeling? Claire didn't understand any of it.

She suddenly received a call on her cell phone. She picked it up and answered. "Hello?"

It was Issei. "Hey, Claire. What's up?"

"Oh, it's you. What do you want?" Claire asked.

"Well, I was wondering, because I want to make it up to you... do you wanna go shopping together, and hang out and stuff?"

Claire thought about it. She needed to go shopping, and she suddenly felt excited about it. "Make it up to me? By going shopping with me?" Claire thought more about it; she couldn't really resist. "Very well, then." She smiled a little. "That sounds nice."

"Awesome! I'll meet you at the shopping center!" Issei hung up and got ready.

[A while later]

Issei was waiting at the shopping center for Claire. He had on causal clothing. He then spotted her approaching him. ' _Wow, she looks nice!'_

Claire was in a dark blue blouse with a white and blue skirt. She looked amazing. "Sorry for the wait." She told him, with a smile.

"No problem at all!" Issei grinned and held Claire's hand in his own as they walked, which she didn't mind.

First, they headed to the shopping mall. Claire had picked out a lot of clothing, all of which would look great on her. "I hope you don't mind paying for all of this." She kept on adding to the pile.

Issei had wide eyes. "Wow! Um...that's a lot, but I think I can handle it." He rubbed the back of his head. _'I hope so, anyway...'_

Claire giggled. "Thank you for buying."

After they rung up the clothes, they headed to several other stores in the district. There was an arcade, pet store, video game & movie store, beauty shop, and several places to eat. Claire wasn't too interested in most of them, but she was hungry for lunch. "Let's go to this restaurant. I haven't eaten here before, but I heard it's quite excellent."

Issei agreed and they headed inside.

It turned out to be a fancy, expensive restaurant. Claire's family was loaded, so it was no problem for her. And with Issei's money combined, they were fine. Issei was glad they ended up sharing the bill, because his wallet was almost destroyed by now. They had delicious foods and drinks, and shared many conversations about tons of things.

"This dish is the definition of exquisite." Claire really enjoyed the food.

"Yeah, this shit is really good." Issei had to agree.

After they finished, they decided to go to the amusement park; it was Issei's idea. They enjoyed activities and things such as bumper cards, merry-go-round, love boats, cotton candy, funnel cake, roller coasters (except the highest one), go-carts, flat rides, train ride, water ride, and the Ferris wheel. They both had a wonderful time.

However, as expected, Claire always wanted to win at just about everything, due to her prideful nature. Issei would usually allow her to win, just so she would smile a lot.

They also took pictures together at the photo booth. Some pictures turned out great, and others had Issei making funny faces, to make Claire giggle.

"I like this one the best." Claire was holding her favorite pic in her hands. It had both of them smiling with their arms around each other.

"Yeah, that's my favorite, too." Issei smiled.

The final plan was to see a movie at the theater. "I'm fine with watching anything, as long as I'm with you." Claire smiled.

Issei grinned. "Sounds good! I'll even pay for the tickets."

"You better." She held his hand as they walked to the theater.

They ended up watching an action/comedy movie. It was cheesy and short, but pretty entertaining overall. Claire snuggled close to Issei and he had his arm around her as they watched it.

After it finished, they exited the theater, hand in hand again. They appeared like a couple at this point. It was almost late at night now.

"That film was quite silly, wasn't it?"

"Yeah, it was. One of the goofiest things I've ever seen!" Issei laughed. "I'll walk you back home."

[After walking]

Once they reached Claire's headquarters, Issei was ready to kiss her goodnight. "Night, Claire!" He puckered up to her.

"Goodnight, Issei." Claire blushed and kissed him. "Thank you for the great time today." She had pretty much forgiven him about the beach incident by now. She entered her headquarters, still thinking about him. _'Issei Hyoudou... You are really something special.'_

* * *

After that date night, Issei and Claire had a nice friendship together. Issei even offered to help Claire and the Slayers battle against the Savages. Although Claire initially refused because he was an outsider, Issei had eventually talked her into letting him help out.

As time past, it became more and more clear that Claire had strong feelings for the Red Dragon Emperor. She was falling for him, like other women, for his strength, courage, kindness, and heart. Plus, he had been impressing her more and more during battles against the Savages.

[Student council room]

It was currently sunset. The Student Council Room was located in the subway of the school's martial arts department. Student Council President and Little Garden's Queen, Claire Harvey, had been unable to concentrate on her work.

Issei was sitting in the chair infront of the computer table. Sitting on his lap, was Claire herself. It was difficult to focus on her paperwork, due to sitting on Issei's lap. She was blushing, but tried to keep her composure. "Issei Hyoudou, I-"

"Don't mind me. Just get comfortable, and you'll get the work done in no time." Issei encouraged her. _'Her body feels so nice...'_ He drooled to himself.

Claire blushed but smiled, and continued with her words. ''...Very well.'' As she sat on his lap, she tried to finish her work.


	3. Chapter 3

Some time later, Issei and Claire were chilling out in a outdoor onsen that night. All they had was the night sky and the sound of bugs. They were both naked in the onsen as they enjoyed the relaxation, holding drinks in their hands and having tons of conversations. They shared kisses once in a while during the night.

After they finished the drinks, Issei had something important to say now. "Claire, I want you to know that...I love ya!" He embraced her.

Claire knew how Issei meant that; it wasn't the creepy kind of 'I love you'. She smiled softly. "Love you too, Issei." She hugged him back. "Thank you... For everything."  
They kissed again and there was a bit of silence.

Issei broke the silence. "Claire, I got a question for you."

"...I'm listening." Claire was intrigued.

"Wanna battle with kisses? Like a contest, I guess you could say." Issei grinned.

Claire was very competitive, and powerful. She was very familiar with competitions and battles, that's for sure. She couldn't decline a challenge, nor have the thought of losing in the end. "You're on. I will be victorious." Claire declared arrogantly, but also blushed a little too.

Issei grinned bigger and got excited. "Hell yeah!"

"The first move is yours." Claire declared with her lips ready for him.

They began making-out in the onsen. It felt amazing, and they had their arms around each other. They shared deep, passionate kisses with tongue. They went at it for quite a while, neither stopping or showing signs of wanting to quit the battle.

Claire pulled away briefly for some air. "Y-You really are something, Issei..." she blushed and said with embarrassment.

"Yup, that's true!" Issei smirked a little, and slipped his tongue in her mouth again.

Claire gasped at this, but regained her composure to continue with all her kissing power.

Issei knew deep down he was going to win, because he was obviously more experience with this stuff. He continued kissing the blonde Prez like there was no tomorrow, and Claire attempted to return everything back. _'Oh man, her mouth is so wet and warm!'_

They kissed deeply as their tongues swirled around and battled in their mouths. They exchanged saliva during this kissing battle. Issei also enjoyed how Claire's large and wet boobies were pressed against his well-toned chest as they kissed.

"I-Issei..." Claire blushed as they swirled their tongues around together. She was having trouble keeping up now. The two were feeling hot inside as they continued kissing and making-out.

Issei did some impressive kissing techniques that Claire wasn't familiar with. It caught her off guard; she struggled to not only keep up with him, but to keep her composure.

Issei finally won when Claire gave in. "I... I surrender. Y-You win." Claire was breathing heavily after she pulled away, her face super red.

Issei smirked as he pulled away too, feeling victorious. "Hell yeah, I win!"

"W-What would you like for winning? I figure you should w-win a reward of some kind..." Claire looked away in embarrassment.

Issei didn't have to think for too long, for he basically knew what he wanted. "Claire Harvey, will you allow me to take your virginity...tonight?" He held her hands in his own, giving them a warm squeeze.

Claire gasped and swiftly looked at Issei directly, completely in shock and surprise. To her, it was similar to a marriage proposal. "Y-You... Issei... I...I-I..." she couldn't really form a whole sentence. Claire nonetheless hesitated to fully answer, a worried look on her face. "Issei..."

Issei managed to calm her down with a gentle kiss.

During the kiss, everything seemed clear to her. She thought about Issei a lot, and he was the 'first' for her in many ways. It only seemed natural for him to take her virginity, of all men. After thinking about it in her head, she accepted. "...A-Alright, let's commence the operation."

* * *

The two went to Claire's headquarters to have sex in bed. It was the place Claire preferred to do it.

Her face dyed a deep crimson, Claire mumbled, "Why do you always snatch away all my firsts…?" Her face turned away in embarrassment.

Issei chuckled. "Well... What are you gonna do?" He had a point. They were both naked and they embraced each other.

If she were to be seen in this state, Claire didn't think she could handle the embarrassment. Thankfully no one would see. _'I realize the truth of this situation. I'm about to lose my virginity, and there's nothing stopping it.'_ Claire asked Issei in a nervous tone, "Please, be gentle with me. It's rather embarrassing to be in this situation..." Claire was red to the max as she slowly closed her eyes. She tried to overcome her fear, embarrassment and doubts. She prepared for a kiss.

 _'She definitely is a beauty.'_ Issei thought as he also closed his eyes and kissed down; their two lips coincide, and their breathing began to hurry up. The feeling of a kiss had reached them.

"Nn, fuu…" Claire's tongue invaded his mouth. Her lips stuffed Issei's lips.

They french kissed, tangled tongues included and saliva exchange job, too. Deep and passionate french kissing at it's best. The kiss lasted awhile, as both were naked and with their arms around each other.

Issei was squeezing her butt during the make-out session. Her butt had less flesh than her breasts, but his fingers still sank into it.

"Mmhmp!" Claire was surprised at Issei's hands on her butt in the kiss. Claire hung her lips against his.

Issei pulled away briefly. "All you need to do is let me make you feel good." Issei said as he resumed the kiss. Lips and lips touch...

 _'This feels nice..._ ' Claire thought as she enjoyed the kiss. Her face turned red as she noticed that she was in the state of pushing down Issei. At the same time, she noticed that Issei is getting excited.

Claire's mouth was warm and wet, so kissing her felt amazing and turned them both on. Her tongue felt good while kissing as well. Tasting her wet and warm mouth with the tongue and saliva included was crazy good.

They repeated a kiss many times over and over. Short kiss, lengthy kiss, several times.

Finally their tongues and lips drew apart, the lengthy kiss ended. After they finished, they sat up on the bed.

"W-What do we do next...?" Claire asked nervously.

Issei focused his attention on Claire's naked breasts. "Titty time!"

Claire blushed madly and nodded slowly. She had her hands covering her breasts, but now she removed them for him. Both her nipples and areola were beautiful.

 _'Whoa, look at how massive her breasts are!'_ A sight that his growing erection showed he was happy with. He decided to have some fun with those large, soft funbags. "I'm going to grope them, Claire." He told her as he was about to go to town!

"Go right ahead. But be g-gentle..." Claire's face reddened more.

On the president's invitation, he wrapped his hands around the two lovely peaks from below and moved his hands in circles. Breasts was as soft as pudding, yet it had an intense elasticity that pushed back at his fingers like springs. When he touched them, he found them to be the perfect level of soft yet also vibrantly elastic. Issei noticed the temperature above the hand.

"Nnaaahhh…nnn. Your hands…Your hands are squeezing my breasts…!" Claire's face flushed and raised eyebrows.

He initially softly touched those soft mounds and lifted them up to check their weight, but then he dug his fingers into the far-too-soft flesh, eliciting the president's moaning voice. But there was no hint of pain in the moan, her skin was trembling a little, and she was obviously aroused.  
"They're so soft, it feels like my hands are sinking into them! I love boobs!" He started groping her breasts even stronger over time. He let his fingers sank into that white flesh like it was a swamp. Issei lost himself in the fluffy softness and smooth skin. The warm body temperature and milk-like aroma only built the passion of his caress. As his hands fondled her soft mounds again and again, he watched them change shape as if sucking in his hand. He was no longer able to control the strength of his hands and his fingers dug even deeper into her flesh. _'I really do love boobies!'_ He was the Oppai Dragon, after all.

"Nnaahh… So-so rough. If you're that rough…"

With all the experience and knowledge he had of breasts, Issei knew exactly how to touch Claire in all the right ways. He grew even more aroused as the boobs seductively changed shape before his eye and he used every piece of knowledge he had to try to draw out as many moans of pleasure as he could. He even rolled her light pink nipples between his fingers until they grew erect.

"Fwah… That…that's amazing… Your fingers feel so good on my nipples…" she felt embarrassed but felt so much pleasure, too.

"Really? Then I'll keep doing it." He responded to her voice by persistently rolling her nipples between his fingers while fondling those large boobies. Those gummy-like points grew to the size of her pinky finger's tip and bent a little. "Claire, your breasts are amazing...!" Watching them was enough to make Issei even hornier. He also kissed her as he continued to knead, to rub, to massage her breasts.

Claire moaned by the touch and kissed back hard. After awhile, Claire broke the kiss. "Nn…ahh… No…this isn't enough. Suck them, Issei. Suck my tits… Suck them as hard as you can…" Her seductive voice asked for even more stimulation to her breasts.

"Okay, I'll suck your tits now!" No man could have refused that request, so of course Issei wouldn't. Unable to restrain his arousal, Issei sucked on one of the erect nipples.

"Kyaaaaaaannnnn!" But as soon as he did, the queen of the school's body gave a large jerk and the stimulation to her aroused nipple brought a damp scream to her lips.

He fondled both her soft mounds while moving his face back and forth between them, licking and sucking the nipples. Each time he licked the tips and each time he sucked the entire areola, an agonized moan would escape her lips.

"Ahn! M-My nipples are my weak spot."

As he dug his fingers in to grope those soft fleshly balls, they grew gradually tighter and pushed back at his fingers. The nipples grew slightly darker and even the areola swelled out as Issei enjoyed the gummy-like texture.

"Nnah…pant, pant…I can't…stand it…" Her voice gradually grew higher pitched. Moisture filled her blue eyes. The dampness of her moans grew and reverberated through the room as she wrapped her arms around his head so he would suck on her nipples even more.

Issei continued to have fun with Claire's unbelievable breasts. Motor-boating them, fondling them, sucking them, kissing them, everything you could imagine. He continued to suck and play with her breasts for several more minutes.

"Kyaaaaaaaaaaa!"

He sucked on both nipples at once with the tits pressed together. He also pressed his fingers on her nipples like buttons. He also motor-boated her! "Brbrbrbrbrbr!" He grinned with his face buried in her soft amazing tits.

"AHHHHHHHH!" The sensations was tough to handle, and Claire moaned loudly.

After he finished, he had a question to ask. "Could you return the favor?" Issei asked with his hands still sinking in her breast flesh.

"...S-Sure... I guess so." She got on her knees, and took Issei's hard cock inside her mouth. She swirled circle around it, and sucked on it, while moving her hand on the shaft. She wasn't good at this, but tried anyway.

Issei moaned lightly at the pleasure of this blowjob. Clarie's mouth and hot breathing felt really good on his dick. Her mouth was so warm and wet. Her tongue felt really good, too.

Claire continued to suck on him, trying her best even though it was her first time doing so. "I can taste some juices on my tongue...a-are you close?" She put it back in and sucked him harder, also fondling his sensitive balls. She continued this for some time.

"C-Claire, I'm gonna cum!" Issei shivered and moaned, then eventually shot the load in her mouth.

"Mmhp!" Claire couldn't swallow everything, but enjoyed the taste. "It's not bad." It tasted good because of Issei being a dragon and a devil.

He then began devouring her gorgeous body. Issei enjoyed Claire's body every which way possible. He rubbed her pussy and rubbed her thighs. He kissed and massaged her all over and enjoyed every inch of her body, especially her breasts.

She shuddered and moaned, dripping wet between her legs. "AHHH~ Issei!"

After seeing this, Issei fingered her pussy. He moved his fingers inside and pleasured her pussy.

"AHHHHHHHHHHHH!" She moaned loud and shivered in delight. It was almost too much.

He fingered and ate out her pussy. He enjoyed the taste of her pussy juices. "Mmh. Peaches." He had his tongue inside and swirled it all-around. He had tasted the juices of tons of chicks before this one.

"AHHHHH!~" Claire moaned. Claire then slowly sat down on Issei's face. She blushed. She pressed her butt into Issei's face, wanting him to lick her pussy more.  
He continued to eat out Claire's pussy, his hands resting on the sides of her ass.

"Ah! Ahn! Don't stop, that feels great! Ah!" Claire had a cute face and moaned.

"Mmhm." He really enjoyed the taste of Claire's wet pussy as he ate her out and fingered her.

"Lick all-around inside of me. A-And don't you dare hold back!" Claire was getting into it.

Issei nodded and he started to move his tongue all-around inside her wet pussy, just as he was told. He ate her out, without mercy.

"Mmhm, you're good at this, Issei...!" Claire moaned in great pleasure and came on his face. "AHHHHH!~"

After that finished, Issei had another idea. "Give me your tits!" He was holding his dick in hand.

Claire laid back for him. "O-okay..."

Issei slid his cock inbetween Claire's breasts. He held them on the sides and started pounded away. "Ahhh!" He moaned at the softness.

Claire blushed madly. "Oh Issei..."

Issei continued thrusting hard, moaning even more. His dick often disappeared inside the large mounds. "They're so soft...so big...ahh!" He moaned and thrusted more, his head now going near her mouth.

Claire licked the tip to add more pleasure. "H-hows this?"

"Ahhhhhh, hell yeah!" Issei shivered and moaned. He thrusted the tip inside her mouth, while pounding harder and his hands squeezing on her breasts, also the nipples were inbetween his fingers. After continuing for awhile, he eventually had an orgasm. "AHHHH!" He came strongly with his nine inch dick buried in her large breasts.

Claire cleaned up and blushed madly. "That was...really something."

After a minute or so, they were ready for the main course.

Issei couldn't be more excited. Because today, his cock would be planted inside her most precious place, of the beautiful Prez.

Claire knew what was coming next. ' _I can't believe he's about to take another one of my first's... He's taken so much already...and now...'_ She blushed madly. "It's embarrassing..." Leaning back she allowed Issei to set himself up to fuck her in the expensive bed.

"It's not embarrassing. You're beautiful." Issei felt it was his duty to take the lead, so he laid ontop of the Claire on the bed while propping himself up with his arms. "Here I go!" He almost had a nose bleed!

Fear overtook Claire's body. ' _Oh god...he's about to...'_ Claire looked away with an extremely embarrassed expression on her face.

At her request of being gentle, Issei wanted Claire to be as comfortable with things as possible. "I'm gonna put it in now." He pressed the head against the tip of her pussy.

"Okay… Ahhhh!" Claire cried out. Claire's revealed pussy felt both the chill of the air and the heat from the penis head. _'I can't believe this is h-happening..._ ' She held onto his hands for support.

Issei breathed heavily from the blissful arousal he felt when invading the female body with his penis, something he has experienced countless times. "Oohhh…wow." Even with all the lubricant stickily covering the soft flesh, his dick still had trouble entering. He pushed in more to break her barrier once and for all. _'Claire Harvey's virginity is mine.'_ He felt a sense of accomplishment. He also cast a Devil spell on his body so he could last longer.

"Ahhhhhhhhhh!~"Claire groaned and gasped at the pain and sensation of becoming an adult. She shot some juice already. "H-how embarrassing..." Claire mumbled.

"That's nothing to be ashamed of! It just means that you're feeling really good... Now let's make you feel much better!" The Red Dragon Emperor slowly started pumping himself into the girl, which caused her to wince in pain. "Are you okay, Claire? D-Does it hurt?" Issei stopped his hips when he found her so tight it hurt the head of his penis. He was worried he would damage her sensitive flesh if he kept going.

Claire answered while holding him in a tight grip. "I-I'm fine. Just…keep going-g."

"O-Oh…sure." He moved his hips at a steady pace. He was patient with her as he waited for her to get used to it.

 _'T-This is incredible. I've never felt this good before...! Ah! It's a feeling I can't believe I've never had before.'_ Claire thought as Issei's ministrations made her moan louder and louder.

Issei continued pounding her, dominating her whole vulva. Issei continued at a decent pace. _'Wow, this is...!_ ' He felt amazing right now. "It should start feeling good soon."

"Ah, hh, hh, hhhhh…" Claire clenched her teeth and endured the unfamiliar sensation of having someone else inside her body. "Kh…ahh…hh...ahhh!" She put her hands on Issei's forearms.

Without rushing or pulling out, Issei rubbed their sensitive flesh together to let the entrance of her tight love tunnel familiarize itself with the head of his cock. "Claire, does it still hurt?" He looked down to the base of her spread thighs and saw his manly cannon halfway buried inside of her pink pussy.

There was still a lot of pain in Claire's voice, but the amount of moisture in her holy tunnel gradually grew. "It d-does... NHAah! Uuh, it hurts." She gave another upset groan and arched her eyebrows. But the pain was not unbearably bad. "S-slow down...! I might spurt again!~" Claire threatened with confidence.

He began thrusting a bit faster now, but not hard. "Ahh…ahhh. Your insides…are sticking to me, Claire!" His erection grew even larger from the pleasant feeling inside her.

"…I-Issei." She looked up at Issei. Various emotions appeared and disappeared in her deep blue eyes. Claire was starting to really get into it herself. "Ahhhh~!" At the moment Claire's legs were wrapped around Issei who pummeled her vagina with fierce strikes. Her face turned more red. "Ahhhhh!" She came on him.

"Ahhhh! Claire!" Issei said as his thrusting continued, feeling her juices on his cock. Issei could sense her delight and he tightened his grip on Claire and deepened his penetration. "Hh…khhhh, ahhhhh." His cock rubbed against every nook and cranny of her vagina. He continued thrusting his cock inside her pussy and bent his body to bring their faces in close. "Ahhh…khhhh, ahhhhh~"

Sweat covered Claire's amazing naked body and her long blonde hair clung to her. She moaned louder.

Issei stuck his fingers in that blonde hair and enjoyed its honey-like smoothness while peering into her beautiful face. "You're starting to relax down here." He began to move back and forth harder and faster now. "Ah, ahn, ahnn…ah." Her vagina's length, its thickness, the strength and frequency with which it wrapped around him, the shape of the folds when it squeezed, and probably even the shape of her pubis, hips, and womb were all a perfect fit for his dick.

It was starting to feel really good for Claire now. Their sex organs had grown accustomed to each other. "Ahn, h-hey. Not so har-…ahhhahn!" Her body was sweating and her breathing got heavy.

He started thrusting a little roughly. "Does it feel super good, Claire?!" Meanwhile, he slowly sped up his hips to drive his ferocious cock into the sensitive flesh surrounding it. "Nn…hnn…"

"Wha-…? O-o course-e...!" Claire gasped and moaned loudly at the thrusting. She had trouble speaking and her eyebrows arched upwards. As the hard penis moved through her vagina, her insides tightened and relaxed around him. "Ah, ah, ahhhn. Hey, I told you…not so har-ahhhhhhhhn!" The prideful Claire had been restraining her voice so far, but now she released a truly sweet cry as her entire body convulsed. Her sexy body bounced around and she could not raise any kind of protest.

Issei enjoyed watching Claire's boobs bounce as he fucked more harder. Confident that she was feeling pleasure, Issei thrusted balls deep. Enjoying himself even more, Issei put his body weight into his hips. As he repeatedly pounded his penis inside her pussy, he could feel her hot juices coating his tightly-wrapped penis."Ahhh...oh G-God!" Issei moaned loud and he suddenly grabbed both of her large breasts. He thrust quickly and as deep as he could.

"Wh-what are you-!? Hh, hhhn~ Wait, ahhhn, wait~!" Claire moaned wildly. "Hahn… Ahahn, nnnn…"

He dug his fingers into her breasts and pushed the protruding nipples back inside the areolae. He played with them wildly, while thrusting hard and fast. "Gahhh!" He pumped his hips with even more force than before, feeling Claire cum on him several times now. He added some twisting and angled movements while penetrating deep inside. He would sometimes stop deep within her and skillfully rub against her cervix, but he generally just thrust his hips like an animal. "Hwah…ahn, hahn, nn…hhh!"

Claire's entire body seemed to convulse. She threw her arms and legs around him. "Nnah!? Kyaaaaaaaaaaaahhhhhhhhhhhhh!" Claire was stammering from the ministrations.

 _'Claire looks like she's about to cum!'_ Issei felt his arousal rise to its peak. He leaned forward and pressed their chests together. His chest was very manly, and it squished her large, soft boobies. "Arghhh!" He began moving his hips more roughly, feeling insane pleasure.

"Ahn! Hhh…ah! Ah, ah, yes, there~" Her huge breasts shook and she seemed to be accepting the penis with her entire body. "Ahn~! Hahn~ …Heeeen. Y-yes, right there."

And they moved their hips with enough harmony to show considerable experience together.

Issei made use of the abnormally wide head of his penis as he thrusted in and then nearly pulling his penis completely out. When he pushed in, the tip would accurately hit her womb. When he pulled out, he would rub at all of the flesh inside and finally try to hit the somewhat tighter entrance. "Your pussy feels... s-so good." Sweat dripped from Issei and he embraced her hot body. "C'mon, let's kiss."

"Hyahhh, ahhhh~!" She wrapped her arms around his neck. They shared a kiss. Claire then pulled away. "Ahhn. There, ahh, yes, there!" The Claire's voice grew even higher pitched from the perfect unity she felt through her vaginal flesh, her body leaking more juices.

Issei was now finally entering his orgasm, and he could feel the juices slowly escaping his body. "I'm about to cum. I'm gonna cum now, Claire! Claire…" His inner love for her amplified the pleasure he felt from the continuous wave-like motions of her vaginal flesh. The urge to ejaculate was several times greater than normal. This is something he felt when he had sex with Rias, Akeno and Asia among others.

"Ahhhhhhn. Ah, nn, nn. You're rubbing…everywhere inside me!" Claire felt her approaching orgasm as well, again. She felt insane pleasure and her entire vagina tried to milk the penis when she sensed it was about to cum. "Ahhn, hyahhn."

Issei's dick got really hot and hard inside Claire's pussy. "I'm about to cum! I'll make sure my cum goes deep inside you as p-possible!" He gave her more pleasure than anyone else could give her.

"Ahhhhh~" She had trouble speaking as she lifted her hips to accept his thick penis inside. Her usually dignified voice melted to a hopelessly seductive tone which made his dick even harder inside. "Bwah, ah, ahh!"

He pressed the head of his penis against her somewhat curved cervix to push through to the other side. Every part of a Claire's body was made to be soft, so even that somewhat hard cartilage-like spot was no match for his forceful masculine hardness. The lid meant to protect her baby garden opened inwards.

"Nfwaaaaaaaaaaaaaahhh…" Claire almost fainted.

"T-This is incredible!" He thrusted and moaned. "A-Are you cumming, Claire?" Issei's thing pushed in as deep as it would go. Their vagina and penis were a perfect match and, when he was inside her down to the base, the flesh stalk would hit her carnal weak point at the perfect angle. He embedded his thick penis head in her G-spot. "Hurry up and cum. C'mon, Claire!"

"Ah, ahn, ahhhn. Ahh~! Ah~!" She remained prideful even now, but not even she could keep up the act. Her face grew sexy as she drowned in sexual pleasure. Her toes curled up on her feet as she locked her leg around his waist. She also gathered strength in the arms around his neck to embrace him with her entire body.

Issei suddenly thought about everyone's reactions to this event. ' _U...Uoooooooh! ...I-I don't care what happens anymore, I'll take responsibility!_ ' He thrust without reservations and came close to climaxing.

Claire was sinking into deep pleasure. "Ahh… Ah, ahh~! "

"OH GOD HERE IT COMMESSSSS!" Issei's penis head spewed a great quantity of hot cum into her womb, filling her to the brim. He came strongly inside her hot, wet, soft and tight pussy like there was no tomorrow. "GAAAHHHHAHHHHHHH!" He had his face buried in her tits as he came inside.

"Kwah…ah, hh, ahhh…!" The lid to her most precious place had been pried open and a sticky dampness had been pumped inside the narrow pathway. Claire could not speak properly as he ejaculated so forcefully it could be heard inside her lower stomach. "Hkh, hhh…"

Meanwhile, Issei was pumping more as he filled up her pussy with a milky liquid and his body was shaking in delight.

With Issei pumping and dumping inside her, her body began to convulse. "Hyah…I-I can't take anymore! My stomach's…already full...!" Claire's orgasm came next, strongly. "HYAHHHHHH-NAAAAAAA~!" Warm fluid sprayed from deep within her young pussy. The juices left her as her body came like crazy and she sprayed pussy juice all over his cock. The orgasm was really strong because Issei's hands were squeezing her breasts at the same time.

Issei pulled back his hips with a 'pop'. When he pulled his penis from her vagina, the hole shrank down again almost immediately and some cum burped out.

Claire laid on her back with her limbs lying limply next to her and all of her muscles twitching, especially in her lower body, a white liquid dripped from her pussy. "Ahh, fwahh… I-I feel so full."

After they cleaned up, they cuddled together in warm pj's. They drifted off into a deep sleep, feeling completely safe and peaceful.

* * *

 **(A/N - Inspired by Karlos1234ify, I will do another chapter to this story. It will be considered a "bonus chapter", and it will consist of Issei in a harem with several girls from the series 'Hundred'. Stay tuned for that!)**


	4. Bonus Harem Chapter

**A/N - Well, here it is: the last chapter. I wasn't planning on doing this originally, but after reading a certain review, I announced at the end of the previous chapter that I would do this after all. If you guys like Issei to have more harems with girls from other universes, I might do more like this in the future. We'll just have to see.**

* * *

Eventually, after Issei stayed in the 'Hundred' universe for quite some time, he managed to build another harem! With this new one included, Issei now had two harems in total, counting his harem from his own universe.

The ladies from 'Hundred' fell for Issei in a similar fashion to how the ladies from his own world fell for him: his dragon genes and his incredible powers!  
Once he had Claire falling for him, it was only a matter of time before Issei would spread his love across the 'Hundred' series. In fact, what Kuroka and Xenovia taught Issei from his universe was how he could use his dragon genes to build up a harem. It definitely worked, that's for sure.

First there was Emilia Hermit, a silver-haired girl from the Britannia Empire and a citizen of the Gudenburg Empire by birth; she was also known as Emilia Gudenburg, the Empire's third princess. Along with her was Claire Harvey, the Red Queen.

Also, there was Karen Kisaragi, Hayato Kisaragi's younger sister who was good friends with the popular idol Sakura Kirishima. Speaking of Sakura, she was also present. Liddy Steinberg and Erica Candle were there, too; they were the Little Garden's student council Vice President's who look up to Claire.  
Miharu Kashiwagi was also there, a very attractive nurse who took care of Karen when she was sick. Claudia Lowetti was present as well, who was Emilia's friend from Gudenburg. And last but not least, Issei got Serbia Notredame Paulo III in his harem; she was an extremely hot beauty and the pope.  
Issei was currently in a large room at night, with all the hot women surrounding him. Emilia, Claire, Sakura, Liddy, Erica, Karen, Miharu, Claudia, and Serbia were all naked and ready for action! Some were laying on mats on the floor, while the rest were laying on the comfy large bed. All of them were looking at Issei with either sexy or cute faces.

The harem king was super excited at the sight before him. "This is fucking paradise!" Issei gave all of his women a long and deep passionate kiss on the lips, one-by-one. Each of them returned the kiss to him with great passion. He also used this time to get used to their bodies; he felt them up, from head to toe. He especially enjoyed Serbia, Miharu, Claire and Liddy...for their large breasts, of course! He sucked and played with them.

After that was finished, he asked all of them to get in groups of three, thus creating several Pleasure Towers.  
He kneed behind the first group of ladies, which consisted of Liddy, Sakura and Karen. First, he inserted his cock inside Liddy's pussy, taking her virginity; he then began thrusting at a decent pace. He drilled each of their pussies in turn, alternating randomly. He had taken the virginities of all three girls. He took a brief break after banging one of their love tunnels for too long.

Sakura screamed in pleasure each time she was penetrated by Issei's big cock. "A-Ahhhhhhhhhn~! It feels so good~!"

Karen moaned out cutely, doing it multiple times. "Nghh! Ahh! Ahhhhh!~"

Liddy loved the feeling of Issei's cock banging her insides. "A-Ahhhhh! N-Nnnnn, ah...!"

Issei continued on for several more minutes, fucking each girl hard, deep and fast once they got used to it. He felt his orgasm approach while fucking Sakura's pussy. "Oh shit, here it comes-NNNGGGGHHHHHHHH!" Issei's cock exploded inside Sakura's wet, hot and tight pussy with the initial load, then he pulled out and spurted more cum inside the pussies of Liddy and Karen, one-by-one.

Issei soon moved on, not wanting to waste anytime. He kneed behind the second group of ladies: Claire, Emilia and Serbia. Issei moved his cock inside Emilia's tight pussy, and pounded her virgin pussy. He banged each girl hard, fast and deep, and switching between the three at random times. He already had Claire's virginity from earlier, but now he had the virginity of Emilia as well.

Claire screamed in ecstasy, never getting enough of him. "I-Issei... Kyaaa!"

Serbia enjoyed everything that was happening with her. "Nghh! It feels incredible...! Keep going...!"

Emilia could barely handle the intense sensation. "I-Issei, it's too good! I love it! Ahhhhhhhh!~"

Issei felt so good that he could cum at any second. He fucked Serbia's pussy like crazy, then at a certain point, he felt his peak rising. "H-Here I cum AGGGAAIINNNN!" He started to cum uncontrollably inside Serbia's amazing pussy, using a good amount of semen. He suddenly pulled out, then began shooting more hot cum inside Emilia's pussy and also Claire's as well.

Issei then got behind the third group: Claudia, Miharu and Erica. Issei pounded Claudia's pussy first, then alternated randomly between the three of them. He took the virginities from all three of them. He pounded each girl without mercy once they got used to it.

Miharu screamed in pleasure. "Oh yes, Issei... your cock is going deep inside me!" She moaned loudly.

Erica had moaned just as loud, enjoying the intense pleasure she was receiving from him. "Ah~! Ahn! Don't stop~!"

Claudia felt like she was getting addicted to Issei's cock, and fast. "Ah... Ahn... Mmm... Ahhhh!"

With having so many tight pussies to fuck, Issei could cum at any second again. While banging Erica's tight pussy, Issei felt his peak rising again. "Here it is-NNNAAAAAAGHHHH!" Issei unleashed a massive load of cum inside Erica, pulsating with each release. He then pulled out after a few seconds and then spurted more cum inside Claudia and Miharu, one-by-one.

With Karen, Claudia, Emilia, Sakura and Erica knocked out, Issei continued on with the remaining women who were ready for another round.  
Issei got them in the last Pleasure Tower lineup. He kneed behind the group, consisting of Liddy, Claire, Serbia, and Miharu. He inserted his cock inside Serbia's pussy first and thrusted at a reasonable pace. He still wasn't quite used to her love tunnel yet. "O-Oh shit, that feels good!" He fucked each of their incredible pussies in turn, alternating randomly.

"Ah...! Yes... yes! More, Issei!" Liddy moaned out loud.

"It feels as good as ever...Kyaaaa!" Claire gasped at the feeling.

"Yes ah yes ah, ah ha ha ha ha!" Miharu was moaning wildly.

"Oh god...Issei, harder...faster! Ah!" Serbia loved Issei's cock.

They all hoped that this could last forever.

Issei continued on, banging them in turn for several minutes. He loved every second, while going hard, deep and fast. He was about to cum again as he picked up the pace, while banging Serbia's pussy for the dozenth time. "Here it c-comes... I'm... I'M CUMMING! HNNGGGHHHH!" Issei erupted inside of Serbia's pussy, flooding her chamber with hot cum. After seconds of shooting inside, he pulled out and shot more cum inside the pussies of the other three as well.

There was one last thing Issei wanted: a tit-fuck session! "Girls, come here." He ordered them to his lard cock on the bed.

"Like so?" Serbia pressed her voluptuous breasts against Miharu's equally impressive breasts, squishing Issei's cock between them in a pillowy embrace. Claire's large breasts then also squished in there, along with Liddy's tits. They all began rubbing against Issei's cock in the middle, having lewd faces.

Issei jolted at this strong sensation. "OH YEAH!" He felt insane amounts of pleasure. ''Hell y-yeah!"

The Hundred women redoubled their efforts. Serbia used a heavy scrubbing motion to get Issei's attention. Her aggression spurred Claire to do the same; they alternated their motions, one pair going up while the other coming down, endlessly caressing the erect cock in titflesh. Miharu rubbed in a similar way that Serbia did, and Liddy seemed to follow Claire's movements with her own.

As he was in this very pleasurable moment for a few more minutes, Issei couldn't hold it in any longer. "Here I-HRGHHHHH!" He came hard, sending cum flying to the furthest reaches of the bed.

"Oh my!" Serbia pressed her tits harder, turning her head up with an open mouth. She caught plenty on her face and tongue, licking some off her lips sensually. Miharu seemed to lick up a bunch of cum as well.

"Mmm...MMMF!" Claire closed her eyes while she was forced to slurp up the remaining few spurts. Liddy also shared some with her.

This last orgasm completely and utterly drained Issei of his energy. "Man, that was...amazing."

All the girls in the room had to agree with him, knocked out or not.


End file.
